Chloroacetaldehyde diethyl acetal

Chloroacetaldehyde diethyl acetal was used as obtained from Aldrich Chemical Company, Inc. 

Chloroacetaldehyde diethyl acetal was purchased from Aldrich Chemical Company, Inc. This substance is listed as an irritant. Proper care should be exercised when handling it. 

The chloromethylpyrimido[5,4-( ]-l,2,4-triazine 86 is an extremely versatile starting material (see Section 10.20.7.2, Equation 12) and was synthesized from the commercially available thiol 151 as shown in Scheme 25. Thus, 6 -methylation of compound 151 gave the sulfide 152, which was nitrosated to allow access to the nitroso-thiomethyl derivative 153. Nucleophilic substitution of the thiomethyl group by hydrazine gave the cyclization precursor 154, which underwent cyclization with chloroacetaldehyde diethyl acetal under acidic conditions to give the chloro-methylpyrimido[5,4-( ]-l,2,4-triazine 86 after workup with aqueous ammonia <2003BML2895>. 

Cautiont Care should be exercised m the preparation of the sodium amalgam since the initial reaction is highly exothermic. This and all subsequent operations should be carried out in a aell-ventilated hood. Chloroacetaldehyde diethyl acetal is an irritant and a mutagen. Care should be exercised in its handling. 

Chloroacetaldehyde diethyl acetal (31.11 g, 0.20 mol) (Note 5) is added by syringe slowly, since the initial reaction is exothermic. The resulting solution is heated at 50°C with stirring for 2 hr. After the solution 1s cooled to room temperature, solvent is removed, first with a rotary evaporator... 

CHLORINATION OF ELECTRON-RICH BENZENOID COMPOUNDS, 67, 222 Chloroacetaldehyde diethyl acetal (621-62-5), 66, 96,100,107 Chloroacetyl chloride Acetyl chloride, chloro- (79-04-9), 69, 2... 

CB2415), and the reaction is capable of numerous variations. Formamide on heating at 175 °C with chloroacetaldehyde diethyl acetal in the presence of ammonia resulted in a 60% yield of imidazole. 

Ceric ammonium nitrate, 55,43 57,115 Chloramine, 58, 35, 36 Chlorine, 55,33, 35,63 Chloroacetaldehyde diethyl acetal, 57, 66 p-Chlorobenzenesulfonyl cyanide, 57, 89 a-Chloroboionic esters, 58, 29 l-Chloro-l,2-dicyanocyclobutane, 58, 68,... 

If chlorine (1 mole) is led, with stirring and cooling, into pure acetaldehyde diethyl acetal (1 mole) at 40-45°, and then sodium ethoxide (1 mole) in anhydrous ethanol is added and the neutral mixture is fractionated, chloroacetaldehyde diethyl acetal, b.p. 157°, is formed in about 70% yield.lp... 

Aminoacetaldehyde diethyl acetal was obtained in 74% yield by heating a methanolic solution of chloroacetaldehyde diethyl acetal with 18 equivalents of anhydrous ammonia in a pressure vessel at 140° for 10 h.505 2-Amino- and 2-(methylamino)-propionaldehyde diethyl acetal were prepared in 55 %and 40 % yield, respectively, under similar conditions.506 Aromatic amines are best brought to this reaction as A-metal derivatives. 

Ethoxy-l-btttyne (5, 592). The preparation of 1-ethoxy-l-butyne from chloroacetaldehyde diethyl acetal has been published. ... 

A number of methyl or benzyl ether derivatives of galactitol have been prepared and converted into acetyl derivatives for mass spectral study. HN.m.r. investigation of the product obtained from chloroacetaldehyde diethyl acetal and galactitol (see Vol. 1, p. 46) has shown it to be the 1,3 4,6-di-0-acetal derivative, which on boiling with ethanolic sodium hydroxide yielded the polycyclic acetal-ether (3). ... 

Chloroacetaldehyde (diethyl acetal) Bromoacetaldehyde (diethylacetal) Salicylaldehyde... 

Treatment of 1,1-dichloroalkanes 231 with -butyllithium (3.0 eq.) produces the lithium acetylides. The chloroacetaldehyde diethyl acetal affords with excess lithium diethylamide lithium ethoxyacetylide via intermediate 232 (Scheme 1-178). ... 

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